Nitrite compound of-2-chloro-6-nitrobenzaldimercurioxide



Patented Mar. 26, 1935 UNITED STATES PA-TE NITRITE COMPOUND OF2-CHLORO-6- NITROBENZALDHHERCURIOXIDE OFFICE J 5 In my 'copendingapplication Serial No. 682,426

Emerlc Havas, South Milwaukee, Wis., assignor to E. I. du Pont deNemours & Wilmington, Del., a corporation of Company, Delaware NoDrawing. Application July 27, 1933, Serial No. 682,427

4 Claims. (Cl. 260 -13) This invention relates to the preparation of thenitrite of 2,-chloro-fi-nitrobenzaldimercurioxide, which is a newcompound useful in'the preparation of 2-chloro-6-nitrobenzaldoxime.

filed of even date herewith, there is described the preparation of a newmercury compound of 2- chlo'ro-G-nitrotoluene which I have: designated2-chloro-6-nitrobenzaldimercurioxide, and which .hasthe followingprobable formula:

I have found that this new mercurysubstitu tion product of2-cl'1loro-6,nitrotoluene can be treated with nitrous acid to form acompound which on further treatmentwithacid will give 2-chloro-fi-nitrobenzaldoxime of good quality and in high yields.

Reissert, in Berichte vVolume 40,. pages 4209-4226 has described thepreparation of a similar compound from unsubstituted o-nitrotoluene.However in view of Reisserts work in which he found that even isomericnitrotoluenes and 2-4 dinitrotoluene did'not give products which wouldreact the same as o-nitrotoluene itself, it was not to be expected thatthe reaction product of 2-chloro-6-nitro-toluene and mercuric oxidewould react with nitrous acid to give a product that could be convertedto 2-chloro-6-,

The following example in which the parts given are by weight will serveto illustrate the prepa-" 7 ration of this new product. I Example v586.5 parts of parts of water, 142 parts of technical sodiumni trite areadded and 1000 parts of 10% sulfuric acid are dropped into the mixtureuntil there is a slight acid reaction to Congo paper. 7 is thenfiltered, washed with water and dried at a low temperature. Theproductisa lightyel- 2-chloro 6 nitrobenzaldimer curioxide are stirredat 22-25 C. with about 4000 The mass low crystalline powder which starts.to decompose at -60 (Land following formula:

HgNOQ The amount of water usedmay vary within wide limits. in theexample, any concentrationfrom 5 to,

or even stronger maybe used, the concentration has, very probably, the:J

While 10% sulfuric acid is specified of the acid to be used depending inpart uponthe amount of water already present.

' While I have given a probable formula for my newcompound, it is not tobe regarded as a limi-' tation on my inventionforwhile'the product byanalysis appears to be substantially a dinitrite Q of2-chloro-G-nitro-benzaldimercurioxide, the" absolute structure of thecompound has not been proved.

What I claim is:

1. The nitrite of 2-chloro-6-nitrobenzaldimercurioxide, obtainable byreacting upon 2- chloro fianitrobenzaldirriercurioxide with nitrousacid. ;2. The dinitrite of 2-chl0ro-6-nitrobenzaldimercurioxide.

acid at atemperature suspension.

4."I'he process which of 15 to 32 C. in aqueous comprises reacting a 2-chloro-6-nitrobenzaldimercurioxide with nitrous acid.- a Y I EMERICHAVAS.'

I, H 40 I 3. The process which; comprises reacting 2-'-fchloro-6-nitrobenzaldimercurioxide with nitrous

